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Hilton Head Island

$169+ Cheap flights from Springfield, MA, MA to Hilton Head Island (HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
— HHH
Nov 4 — Nov 111
Tue 11/4
Tue 11/11
1 adult, Economy
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Cheapflights Tip: The best prices from Springfield to Hilton Head Island are usually found in December or October, booked 49 days in advance, depart on a Saturday or Tuesday and return on a Monday

Cheap flight deals from Springfield to Hilton Head Island

Keep the following information in mind while searching for Springfield to Hilton Head Island flight deals. Data was last updated October 5, 2025.

Round-trip from

$249
(American Airlines)

One-way from

$169
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$334
From Springfield to Hilton Head Island
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One-way flight from Springfield to Hilton Head Island
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Highest demand for flights based on searches. 15% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Springfield to Hilton Head Island

Cheapest flights from Springfield to Hilton Head Island
Explore the most affordable flight options available from Springfield to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2025.

This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amBDL - HHH
1 stop4h 46mAmerican Airlines
Tue 11/47:07 pmHHH - BDL
1 stop4h 51mAmerican Airlines
Deal found 10/3$249
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amBDL - HHH
1 stop4h 46mAmerican Airlines
Mon 11/37:07 pmHHH - BDL
1 stop4h 51mAmerican Airlines
Deal found 10/3$274
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:30 amBDL - HHH
1 stop5h 16mAmerican Airlines
Sat 10/185:57 pmHHH - BDL
1 stop5h 04mAmerican Airlines
Deal found 10/4$284
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:50 amBDL - HHH
1 stop6h 26mAmerican Airlines
Sat 1/36:13 pmHHH - BDL
1 stop6h 05mAmerican Airlines
Deal found 10/5$433
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:00 amBDL - HHH
1 stop4h 44mAmerican Airlines
Sat 1/36:13 pmHHH - BDL
1 stop6h 05mAmerican Airlines
Deal found 10/5$458
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:30 amBDL - HHH
2 stops9h 02mAmerican Airlines
Mon 11/37:07 pmHHH - BDL
1 stop4h 51mAmerican Airlines
Deal found 10/3$479

Cheapflights Fare Finder

 
Customize your flight search to find flights from Springfield to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 5, 2025.
Use the filters below to find and compare flights from Springfield to Hilton Head Island that are best for you.

Fly from

Springfield

Fly to

Hilton Head Island

Route

Depart

Return

Price

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 10/31

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

Tue 11/4

7:07 pm-11:58 pm

1 stop4h 51m

$249

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Mon 10/27

6:30 am-11:32 am

1 stop5h 02m

Hilton Head Island

Mon 11/3

7:07 pm-11:58 pm

1 stop4h 51m

$274

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 10/15

5:30 am-10:46 am

1 stop5h 16m

Hilton Head Island

Sat 10/18

5:57 pm-11:01 pm

1 stop5h 04m

$284

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 1/1

9:59 am-2:16 pm

1 stop4h 17m

Hilton Head Island

Sun 1/4

6:13 pm-12:18 am

1 stop6h 05m

$378

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 12/31

7:50 am-2:16 pm

1 stop6h 26m

Hilton Head Island

Sat 1/3

6:13 pm-12:18 am

1 stop6h 05m

$433

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 10/31

6:00 am-3:02 pm

2 stops9h 02m

Hilton Head Island

Mon 11/3

3:27 pm-11:44 pm

2 stops8h 17m

$448

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 12/31

7:50 am-2:16 pm

1 stop6h 26m

Hilton Head Island

Fri 1/2

6:13 pm-12:18 am

1 stop6h 05m

$518

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Mon 12/29

6:00 am-10:44 am

1 stop4h 44m

Hilton Head Island

Sun 1/4

6:13 pm-12:18 am

1 stop6h 05m

$523

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 11/19

12:38 pm-6:37 pm

1 stop5h 59m

$169

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 10/11

6:00 am-11:32 am

1 stop5h 32m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Best time to book a flight from Springfield to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Springfield with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Springfield to Hilton Head Island

How far ahead should I book a flight from Springfield to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from Springfield to Hilton Head Island. Price data was last updated on October 3, 2025.

Booking 49 days in advance of your planned departure date is, on average, the best time to get cheap flights from Springfield to Hilton Head Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated October 5, 2025.
Read through reviews of airlines operating flights from Springfield to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,041 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.2

Comfort

7.2

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,041 reviews
American Airlines
7.2
Good
11,041 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.2

Comfort

7.2

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Springfield to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilton Head Island from Springfield?

    Most people fly into Hilton Head Island (HHH) if they book a flight to Hilton Head Island from Springfield. On average, Hilton Head has 0 inbound flights from Springfield per day from 5 airlines. Hilton Head Island is conveniently located just 3.3 mi from Hilton Head Island’s city center.

  • How long is the flight from Springfield to Hilton Head Island?

    A quick flight from Springfield to Hilton Head Island can take about 4h 46m. American Airlines provides one of the quickest options available for as low as $249. Springfield and Hilton Head Island are separated by a distance of 802 mi.

  • Can I find deals for flights from Springfield to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Springfield to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Springfield to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Springfield to Hilton Head Island.

  • Can I find deals for business class flights from Springfield to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Springfield to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Springfield to Hilton Head Island?

    Currently, January is the cheapest month in which you can book a flight from Springfield to Hilton Head Island (average of $275). Flying from Springfield to Hilton Head Island in March is currently the most expensive (average of $479). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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